vestipitant   Click here for help

GtoPdb Ligand ID: 5757

Synonyms: GW597588B
Compound class: Synthetic organic
Comment: Vestipitant is an investigational NK1 receptor antagonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 35.58
Molecular weight 491.18
XLogP 5.54
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Fc1ccc(c(c1)C)C1CNCCN1C(=O)N(C(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)C
Isomeric SMILES Fc1ccc(c(c1)C)[C@H]1CNCCN1C(=O)N([C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)C
InChI InChI=1S/C23H24F7N3O/c1-13-8-18(24)4-5-19(13)20-12-31-6-7-33(20)21(34)32(3)14(2)15-9-16(22(25,26)27)11-17(10-15)23(28,29)30/h4-5,8-11,14,20,31H,6-7,12H2,1-3H3/t14-,20-/m1/s1
InChI Key SBBYBXSFWOLDDG-JLTOFOAXSA-N
References
1. Brocco M, Dekeyne A, Mannoury la Cour C, Touzard M, Girardon S, Veiga S, de Nanteuil G, deJong TR, Olivier B, Millan MJ. (2008)
Cellular and behavioural profile of the novel, selective neurokinin1 receptor antagonist, vestipitant: a comparison to other agents.
Eur Neuropsychopharmacol, 18 (10): 729-50. [PMID:18657401]
2. Di Fabio R, Griffante C, Alvaro G, Pentassuglia G, Pizzi DA, Donati D, Rossi T, Guercio G, Mattioli M, Cimarosti Z et al.. (2009)
Discovery process and pharmacological characterization of 2-(S)-(4-fluoro-2-methylphenyl)piperazine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethylphenyl)ethyl]methylamide (vestipitant) as a potent, selective, and orally active NK1 receptor antagonist.
J Med Chem, 52 (10): 3238-47. [PMID:19388677]
3. Ratti E, Carpenter DJ, Zamuner S, Fernandes S, Squassante L, Danker-Hopfe H, Archer G, Robertson J, Alexander R, Trist DG et al.. (2013)
Efficacy of vestipitant, a neurokinin-1 receptor antagonist, in primary insomnia.
Sleep, 36 (12): 1823-30. [PMID:24293756]
4. Reddy GK, Gralla RJ, Hesketh PJ. (2006)
Novel neurokinin-1 antagonists as antiemetics for the treatment of chemotherapy-induced emesis.
Support Cancer Ther, 3 (3): 140-2. [PMID:18632487]